This research proposes objective measures to evaluate product designs through style quantification. To do that, five tasks were conducted: first, yearly car models were collected. Second, design elements were extracted. Third, a style analysis was conducted through similarity calculation and visual significance identification. Fourth, styling strategy positioning of the yearly car design models was analyzed. Lastly, a genetic algorithm was used to synthesize the car designs that maintain brand’s unique style. From these five tasks, the styling strategy can be quantitatively analyzed and be implemented to automatically synthesize optimized design alternatives. In addition, research results and in-depth interviews with professional designers from diverse nationalities confirmed the validity of this research. The results of the research open up new possibilities for making more effective strategic design decisions for managerial decisions through quantitative analysis of styling and provide new insights that were not possible to discover before. Based on this research, researchers and designers can empirically analyze the influence of styling on car design industries, the effect of the family look within car brands, visual significance of design elements and the design trend transitions to grope for a more effective design management.